After losing his house in a divorce settlement, Cleveland moves to Virginia and manages to rekindle an old flame with his high school sweetheart.

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Cleveland blows his chance to escort his new stepdaughter to a dance when he accidentally runs over the family dog.

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Cleveland gets Lester's son Ernie to become Cleveland Jr's friend, but later accidentally gets Ernie taken away from Lester by Child Services.

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Tim gets Cleveland a job as a cable telemarketer. But when Cleveland does a better job than him, Tim wishes bad things on Cleveland.

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Cleveland is embarrassed when Cleveland Jr. publicly announces that he will remain a virgin. But when he discovers how embarrassed Cleveland is, he vows to lose it.

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Cleveland is upset when he finds out that Donna is still attending a single mothers' support group in order to have a good time. Meanwhile, Cleveland Jr. runs for student council president with Rallo as his adviser.

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Cleveland celebrates his first Thanksgiving with his new family, including his own parents Cookie and Freight Train as well as Donna's Auntie Momma who all make a surprise visit to shake things up in Stoolbend. However, the holiday gets complicated when Roberta and Federline decide to celebrate on their own, and Cleveland discovers a surprising secret about Auntie Momma that changes his impression of her forever

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Rallo conspires to kick Cleveland out of his mom's bed so that he can have her all to herself, while Roberta blows off her job of keeping an eye on Cleveland Jr. while on a field trip to Washington D.C..

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Cleveland gets drunk as a Santa Claus and shatters Rallo's Christmas by telling him that his biological father is a deadbeat.

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Cleveland convinces Junior to play for the high school baseball team, but can't hide his embarrassment after he finds out that he is terrible.

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When Roberta's new teacher encourages Roberta to alter her appearance, Cleveland Jr. befriends the disguised Roberta and falls in love with her. Meanwhile, Cleveland comes up with an interesting new invention.

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Cleveland tries to help some troubled teens at the high school get on the right path, but doesn't realize that in the process he's become a drug dealer.

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After Cleveland accidentally discovers Holt's embarrassing secret, he sets Holt up on a date with a woman who turns out to be abusive. Meanwhile, Rallo waits for Cleveland Jr. to pass his pet fish.

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Cleveland Jr. vows revenge on his father after he gets him a job at the Broken Stool but later conspires to get him fired.

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Cleveland takes Roberta on a belated honeymoon to New York, but Cleveland spends more time with his friends than her. Meanwhile, the kids try to sell a pilot to MTV, and Coach McFall tries to "rekindle a romance" with Tyne Daly.

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Cleveland is hailed as a hero after he protects his wife from a robber at an ATM--even though that isn't exactly what really happened.

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Donna becomes angry when Cleveland experiences unexpected grief at his ex-wife Loretta's funeral.

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Cleveland begins pimping out Terry for bachelorette parties as a "cable guy," and Cleveland Jr. gets on the bad side of Stoolbend's top rapper when he takes an interest in his girlfriend.

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Cleveland and Lester are ordered by a judge to work together on a float for the Stoolbend Unity Parade after they get in a fight, while Rallo launches a plan to steal Lester's Confederate flag.

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After Cleveland loses Roberta's college fund to a crooked casino owner, he is forced to resort to extreme measures to get the money back.

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Cleveland's parents announce they are getting married and moving to Stoolbend. Cleveland Jr., fresh off inheriting his mom's fortune, offers to pay for the wedding. But can Cleveland and Freight Train play nice and get through it?

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